Diisopropylethylamine → HCID 66697182, compound

HRID 2096729Notes

Reaction equation

HRID 2096729 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](O)=[O:7])=[CH:4][C:3]=1[CH:11]([CH3:30])[C:12]([OH:29])([C:17]1[CH:18]=[CH:19][C:20]2[O:25][CH2:24][C:23](=[O:26])[N:22]([CH3:27])[C:21]=2[CH:28]=1)[C:13]([F:16])([F:15])[F:14].[CH3:31][O:32][C:33](=[O:41])[CH2:34][CH:35]1[CH2:40][CH2:39][NH:38][CH2:37][CH2:36]1.C(N(C(C)C)C(C)C)C.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1>O1CCCC1>[CH3:31][O:32][C:33](=[O:41])[CH2:34][CH:35]1[CH2:36][CH2:37][N:38]([C:6](=[O:7])[C:5]2[CH:9]=[CH:10][C:2]([Cl:1])=[C:3]([CH:11]([CH3:30])[C:12]([OH:29])([C:17]3[CH:18]=[CH:19][C:20]4[O:25][CH2:24][C:23](=[O:26])[N:22]([CH3:27])[C:21]=4[CH:28]=3)[C:13]([F:15])([F:14])[F:16])[CH:4]=2)[CH2:39][CH2:40]1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 1515259Methyl 4-piperidineacetateHCID 66697185HCID 66697185, compound

Product 1

HCID 66697182HCID 66697182, compoundYield 84.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-chloro-3-[3,3,3-trifluoro-2-hydroxy-1-methyl-2-(4-methyl-3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)-propyl]-benzoic acid (74 mg) in tetrahydrofuran (0.63 ml) were added 4-piperidine acetic acid methyl ester (32 mg), N-ethyldiisopropylamine (65 mg) and benzotriazol-1-yl-oxy-tris-(dimethylamino)-phosphonium hexafluorophosphate (BOP, 113 mg). The mixture was stirred at room temperature for 18 h and then concentrated to dryness. The product was purified by chromatography (SiO2, CH2Cl2/MeOH 1:0=>9:1) to give the title compound (82 mg) as colorless foam. MS (m/e)=583.2 [M+H+].

Workup

  1. concentrationconcentrated to dryness
  2. customThe product was purified by chromatography (SiO2, CH2Cl2/MeOH 1:0=>9:1)

Sources & evidence

ORD record
ord-7ca71d096c924497b6d80abae3d1630a
Source dataset
uspto-grants-2013_05
Patent number
US08450313B2

Reaction notes

Loading…